[(2R,3R,4S,5R,6R)-5-hydroxy-2-[[(3S,5R,8S,9R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-6-methyloxan-3-yl] acetate

Details

• Internal ID: 3005bab0-cf1a-4e37-bb45-5484d09d87b4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-5-hydroxy-2-[[(3S,5R,8S,9R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-6-methyloxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@H]4[C@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O
• InChI: InChI=1S/C32H48O9/c1-17-26(35)27(37-5)28(40-18(2)33)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h14,17,20-24,26-29,35-36H,6-13,15-16H2,1-5H3/t17-,20-,21+,22-,23-,24+,26-,27+,28-,29+,30+,31-,32+/m1/s1
• InChI Key: UYQMTWMXBKEHJQ-QKDXOXSGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₉
• Molecular Weight: 576.70 g/mol
• Exact Mass: 576.32983310 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.8222	82.22%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8454	84.54%
OATP2B1 inhibitior	-	0.5795	57.95%
OATP1B1 inhibitior	+	0.9280	92.80%
OATP1B3 inhibitior	+	0.9726	97.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.7017	70.17%
P-glycoprotein inhibitior	+	0.7106	71.06%
P-glycoprotein substrate	+	0.7677	76.77%
CYP3A4 substrate	+	0.7204	72.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.9471	94.71%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9087	90.87%
CYP2C8 inhibition	-	0.6647	66.47%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4628	46.28%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9396	93.96%
Skin irritation	+	0.4943	49.43%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3659	36.59%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7551	75.51%
skin sensitisation	-	0.9150	91.50%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7718	77.18%
Acute Oral Toxicity (c)	I	0.8422	84.22%
Estrogen receptor binding	+	0.7323	73.23%
Androgen receptor binding	+	0.8119	81.19%
Thyroid receptor binding	-	0.6086	60.86%
Glucocorticoid receptor binding	+	0.7387	73.87%
Aromatase binding	+	0.6916	69.16%
PPAR gamma	+	0.6104	61.04%
Honey bee toxicity	-	0.6491	64.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9692	96.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.02%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.49%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.84%	100.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	94.86%	81.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.32%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.51%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.30%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.90%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.81%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.49%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.59%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.53%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.50%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.20%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	86.76%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.57%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.10%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.72%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.70%	97.36%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.49%	91.38%
CHEMBL340	P08684	Cytochrome P450 3A4	83.11%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.40%	93.04%
CHEMBL4208	P20618	Proteasome component C5	80.99%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.09%	97.14%

Plants that contains it

• Adenium obesum

Cross-Links

• PubChem: 162887601
• LOTUS: LTS0253331
• wikiData: Q105281842